It happens all the time. I once helped a Cesna pilot who arrived in Haiti without funds and no gas. I provided repatriation funds, but he did not use it all. left assuring me he had enough gas, but ran out near Cuban territorial waters. The Cubans rescued him from the sharks. It would probably have been better for the gene pool to have left him to his fate! Also, when there was a crisis and no commercial flights would enter Haiti, a money hungry pilot chartered a DC-3, loaded up with those desperate to leave and the mail. Ran out of fuel over the Bahamas, did a beautiful crash landing in shallow water, everybody happy sitting on the partly submerged wings or nearby island. They and mail promptly rescued, and everybody happy except recipients of water logged mail. There are crazy, or incompetent pilots everywhere.